(3-Butoxy-5-hydroxymethyl-phenyl)-methanol → 5-Butoxyisophthalaldehyde

Participants

Reaction Steps

(5-Butoxy-1,3-phenylene)dimethanol (0.24 g, 1.15 mmol) and CH2Cl2 (10 mL) were added to a round-bottom flask. To the solution was added PCC (0.74 g, 3.45 mmol), and the reaction was stirred at rt for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (90% hexanes/EtOAc) afforded the desired product (0.18 g, 44%, 3 steps) as a white semi-solid. 1H NMR (300 MHz, CDCl3) δ ppm 9.99 (s, 2H), 7.89 (s, 1H), 7.58 (s, 21-1), 4.03 (t, J=6.6 Hz, 2H), 1.77 (quint, J=6.6 Hz, 2H), 1.47 (sext, J=7.2 Hz, 2H), 0.94 (t, J=7.5 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ ppm 191.3, 160.6, 138.6, 124.2, 120.1, 68.9, 31.3, 19.4, 14.1.

Provenance & Evidence